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Synthesis method of compound with biphenyl dimer structure

A biphenyl dimer and synthesis method technology, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of low yield, difficult purification, high cost of raw materials, etc.

Active Publication Date: 2020-07-07
JIANGSU HECHENG ADVANCED MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention application with the publication number CN106608842A discloses a synthesis method of a compound having a biphenyl dimer structure, but the yield of the method is low, the raw material cost is high, and purification is difficult. In view of the fact that the dimer has a high practical Therefore, it is necessary to develop a synthetic method with low raw material price, high yield, convenient purification and suitable for industrialization.

Method used

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  • Synthesis method of compound with biphenyl dimer structure
  • Synthesis method of compound with biphenyl dimer structure
  • Synthesis method of compound with biphenyl dimer structure

Examples

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Embodiment 1

[0035] 1) Add 192.5g Mg and 2g iodine into a 5L reaction flask, fully dissolve them in 2.5L tetrahydrofuran, and add dropwise 1 / 3 of 50mL 1,5-dibromo-pentane and 250mL tetrahydrofuran The mixed solution formed by mixing is heated to reflux after the reaction is initiated, and the remaining mixed solution is added dropwise, and the reaction is refluxed for 6 hours. The temperature is controlled at 35° C., and the mixed solution obtained by dissolving 250 g of p-bromo-benzaldehyde in 250 mL of tetrahydrofuran is added dropwise. Reaction for 3 hours;

[0036] After the reaction, add 700mL of dilute hydrochloric acid with a concentration of 10% dropwise to the reaction solution, adjust the pH of the reaction solution to below 2, and control the temperature of the reaction solution below 30°C, add 2L of water to dilute, and extract with ethyl acetate , combined the organic layers, and the organic layer was washed with saturated aqueous sodium bicarbonate until the pH was 6-7, then ...

Embodiment 2

[0040] 1) Add 192.5g Mg and 2g iodine into a 5L reaction flask, mix well with 2.5L tetrahydrofuran, and add dropwise 1 / 2 of 50mL 1,5-dibromo-pentane and 250mL tetrahydrofuran under the condition of nitrogen protection Mix the mixed solution formed, after initiating the reaction, heat up to reflux, add dropwise the remaining mixed solution, reflux reaction for 6 hours, control the temperature at 45°C, add dropwise the compound (4-bromobenzaldehyde ) The mixed solution obtained was reacted for 4.5 hours;

[0041] After the reaction, add 700mL of dilute hydrochloric acid with a concentration of 10% dropwise to the reaction solution, adjust the pH of the reaction solution to below 2, and control the temperature of the reaction solution below 30°C, add 2L of water to dilute, and extract with ethyl acetate , combined the organic layers, and the organic layer was washed with saturated aqueous sodium bicarbonate until the pH was 6-7, then washed with water until the pH was neutral, dr...

Embodiment 3

[0045]1) Add 144g Mg and 2g iodine into a 2.5L reaction flask, mix well with 1L ether, and add 1 / 3 of 12.3mL 1,5-dibromo-pentane and 65mL tetrahydrofuran dropwise under the condition of nitrogen protection The mixed solution formed by mixing is heated to reflux after the reaction is initiated, and the remaining mixed solution is added dropwise, and the reflux reaction is carried out for 6 hours. The temperature is controlled at 25°C, and the mixed solution obtained by dissolving 185g (4-bromobenzaldehyde) in 185mL tetrahydrofuran is added dropwise. Solution, reacted for 3 hours;

[0046] After the reaction was finished, 700 mL of dilute hydrochloric acid with a concentration of 10% was added dropwise to the reaction solution, the pH of the reaction solution was adjusted to below 2, and the temperature of the reaction solution was controlled to be 30° C., diluted with 1 L of water, extracted with ethyl acetate, The organic layers were combined, and the organic layer was washed ...

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Abstract

The invention provides a synthesis method of a compound with a biphenyl dimer structure as shown in a formula A which is described in the specification. According to the synthesis method, 1,5-dibromo-pentane and 4-bromobenzaldehyde are used as raw materials, and the compound shown in the formula A is prepared through the steps of Grignard reaction, coupling and the like. The method is low in raw material price, high in yield, convenient to purify and suitable for industrial production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing a compound with a biphenyl dimer structure. Background technique [0002] It is well known that the flexo-electro-optic effect can be used as a mode for liquid crystal displays. The most common examples of this effect are the ULH and USH effects. The response speed of the liquid crystal device using the ULH mode reaches 100 microseconds. Compared with the ULH mode, the USH mode can achieve a better dark state, and at the same time can obtain a wide viewing angle range. The traditional liquid crystal display mode requires the liquid crystal material to have a large dielectric anisotropy value in order to reduce the driving voltage of the display. The ULH / USH mode is different. In order to prevent the helical structure of the liquid crystal from unraveling under the electric field, the liquid crystal material is often required to have a dielectric anisot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/51C07C253/30C07C33/46C07C29/64C07C25/18C07C17/35
CPCC07C253/30C07C29/64C07C17/35C07C33/46C07C25/18C07C255/51
Inventor 赵李亮徐爽
Owner JIANGSU HECHENG ADVANCED MATERIALS
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